Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124
Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124

Experience a private 2-day sailing trip from Milos to Kimolos and Polyaigos, with swimming, onboard meals, and nights under the stars, led by expert crew.

The Milos: 2-Day Private Sailing Trip Milos-Kimolos-Polyaigos offers a personalized escape into Greece’s stunning Cyclades. Departing from Adamas port in Milos, this cruise is designed for those seeking an intimate, flexible experience on the water. The entire trip lasts 2 days, with options to customize the itinerary, making it ideal for travelers who want a tailored journey.
What sets this tour apart is the private group setup, ensuring exclusivity and a focus on your preferences. Led by a dedicated skipper and hostess, the trip includes crystal-clear swimming spots, onboard meals, and the chance to spend a night under the stars in Kimolos. This experience suits travelers who enjoy comfort, natural beauty, and a personal touch.
While the tour is not suitable for non-swimmers or those prone to seasickness, the overall pace is relaxed, and the crew’s flexibility enhances the trip’s appeal. For anyone looking to explore the Cyclades in a more intimate setting, this private sailing trip offers a fantastic blend of adventure, relaxation, and authentic Greek charm.
You can check availability for your dates here:
Enjoy being on the water? Here are other boat experiences we've looked into in Adamantas

The tour begins at Puerto Café in Adamas, where a hostess wearing the company’s ID welcomes you onboard. It’s recommended to arrive 20 minutes early for a smooth boarding process. The coordinates 36.7242, 24.4450 make finding the meeting point straightforward. From here, the captain and crew set off on your private cruise, starting from the lively port of Milos.
This initial step is simple and convenient, especially as the trip is exclusive to your group, offering a stress-free start to your adventure. The meeting point’s central location also makes it accessible from most accommodations on the island.

The itinerary is flexible but typically includes some well-known highlights. The group will visit Kleftiko, famous for its spectacular sea caves and clear waters. Here, plenty of time is allocated for swimming and snorkeling inside the caves, which are among the most photographed spots in the Cyclades.
Stops also include Gerakas and Tsigrado, two beautiful beaches accessible only by boat or on foot, known for their secluded charm and crystal waters. These locations provide excellent opportunities for relaxing swims, with the crew ensuring safety and comfort. The skipper is attentive and willing to adapt the schedule based on weather and your preferences.

In the afternoon, the journey continues towards Kimolos, an island celebrated for its authentic Greek atmosphere. Here, travelers can choose to go for a walk ashore or enjoy a dining experience in local taverns. Spending the night onboard under the night sky in Kimolos creates a peaceful, intimate setting, far from busy tourist spots.
Kimolos offers a quieter, more traditional vibe compared to Milos, making it perfect for those wanting to experience local life. The crew manages the logistics, so you can focus entirely on unwinding and soaking in the Aegean ambiance.
More Great Tours NearbyThe second day features a visit to Polyaigos, a protected island famous for its turquoise waters and untouched scenery. This destination is known for being one of the most pristine in the Cyclades, offering some of the clearest waters for swimming and snorkeling.
The crew takes care of the details, and the itinerary can be flexible to match your interests. After spending time in Polyaigos, the boat sails back towards Milos, ending the trip with relaxed cruising and more opportunities to enjoy the scenery.
Drawn to sailing? We've examined these other wind-powered adventures in Adamantas

The dedicated skipper and hostess are central to this experience, providing personalized attention and making sure every detail is taken care of. The captain’s expertise allows the itinerary to be tailored to your preferences, whether that means more time in certain spots or specific activities like snorkeling or relaxing on deck.
The crew’s friendly approach ensures a comfortable and enjoyable atmosphere, making this cruise feel exclusive and intimate. Their knowledge of the islands and water conditions enhances safety and maximizes enjoyment.

One of the tour’s appealing features is the delicious onboard meals and drinks, included in the price. The crew prepares refreshing drinks and tasty meals during your trip, allowing you to relax and focus on the scenery without worrying about extra costs.
This all-inclusive approach simplifies logistics, especially since you won’t need to carry food or drinks ashore. The quality of onboard offerings complements the stunning scenery, making every moment more enjoyable.
The tour is designed for comfort but requires some basic preparations. Travelers should bring a passport or ID card, hat, swimwear, and sunscreen to stay protected under the Greek sun. The itinerary is flexible, and the crew can adapt plans based on weather and your preferences.
Since the cruise is not suitable for non-swimmers or those prone to seasickness, it’s essential to consider personal comfort with the sea. The private nature of the trip means there’s no large group, allowing for a more relaxed pace and personalized experience.

The entire experience is organized by Trion Yachting, ensuring a smooth and professional operation. The private group setup guarantees exclusivity, and you can reserve with confidence, thanks to the full refund policy if canceled up to 24 hours in advance.
Reservation is flexible with the pay later option, letting travelers secure their spot without immediate payment. This flexibility is helpful for planning your trip amidst other arrangements.
This private sailing trip shares some features with other luxury and semi-private tours in Greece, such as full-day sailboat tours with lunch in Milos, or small-group cruises with meals and drinks.
However, what makes this specific tour stand out is its tailored itinerary, exclusive private setting, and the overnight stay in Kimolos, offering a more intimate experience than larger group excursions.
This cruise is best suited to travelers who value privacy, personalized service, and flexible plans. It’s ideal for those who enjoy swimming, snorkeling, and relaxing onboard, as well as for anyone looking to sleep in a peaceful setting under the stars.
Since it’s not suitable for non-swimmers or seasick-prone individuals, it’s important to consider personal comfort with open water. The dedicated crew helps create a smooth, memorable trip, making it perfect for couples, friends, or small families seeking a tranquil, authentic Greek sailing experience.
Milos offers convenient access for this sailing trip, with Adamas port as the starting point. Its lively atmosphere, combined with easy access to the water, makes it an ideal departure point. The central location on the island simplifies logistics and enhances the overall experience.
The tour maximizes what Milos and nearby islands have to offer, providing a luxurious yet authentic way to explore the Cyclades. The personalized approach ensures you see the highlights while enjoying the comfort of a private yacht.
The Milos: 2-Day Private Sailing Trip delivers a balanced mix of adventure and relaxation. The focus on a private, customizable experience means you can enjoy the Greek islands on your own terms, with delicious onboard meals and a peaceful overnight in Kimolos.
While the trip isn’t suited for non-swimmers or those sensitive to seasickness, the expert crew’s care and flexibility help make this a memorable journey for those who love sailing, swimming, and authentic island life. If you seek a luxurious, intimate way to explore the Cyclades, this private sailing adventure is a compelling choice.
Is this tour suitable for non-swimmers?
No, this tour is not suitable for non-swimmers, as swimming and snorkeling are central activities.
What should I bring?
Travelers should bring a passport or ID, hat, swimwear, and sunscreen to stay protected during the trip.
Can I customize the itinerary?
Yes, the skipper is happy to adapt the route and activities based on your preferences, making the experience highly personalized.
How do I meet the crew?
The crew waits at Puerto Café in Adamas, and it’s recommended to arrive 20 minutes early for a smooth boarding.
What is included in the onboard meals?
All meals and drinks are included with no hidden costs, providing a relaxed, all-inclusive experience.
How long does the cruise last?
The entire journey lasts 2 days, with opportunities for swimming, relaxing, and overnight stays.
Is the trip weather-dependent?
Yes, the itinerary can be adapted based on weather and sea conditions for safety and comfort.
Can I reserve now and pay later?
Yes, there is a reserve & pay later option, allowing you to secure your spot without immediate payment.